Cage plays Roy Waller, an obsessive-compulsive, agoraphobic, germaphobic con-artist residing in Los Angeles. His partner is Frank Mercer (Rockwell). The two operate a fake lottery, selling overpriced water filtration systems to unsuspecting customers; in the process, Roy has collected over one million dollars and has developed a crush on Kathy (Sheila Kelley), a cashier at a local supermarket. Roy was married long ago; his wife, Heather (Melora Walters), was pregnant at the time he divorced her. After Roy has a violent panic attack, Frank insists he see a psychiatrist. The psychiatrist, Harris Klein (Bruce Altman), contacts Heather, and reveals that Roy has a daughter, Angela (Lohman). Not long afterwards, Angela turns up on Roy's doorstep. It seems she wants to get to know the father she never had, and also, that she wants in on his and Frank's upcoming con...

This film provides examples of:

Babies Ever After: The last shot of the movie is of Roy standing with his new wife, Kathy, who is now pregnant with his child.

Bavarian Fire Drill: The final part of the last major con. Frank's allies trick Roy into thinking that he's been arrested for Chuck Frechette's murder. Fearing for Angela (who he thinks is on the run from the police), he tells Dr. Klein the passcode to his bank account and has him pass it on to Angela so that she'll have enough money to escape. Armed with his passcode, Frank, Dr. Klein, and "Angela" (who isn't really Roy's daughter) steal all the money from Roy's account.

Bikini Bar: Roy and Frank go to one for their first meeting with Chuck Frechette.

Bittersweet Ending: It starts out looking like a textbook case of a Downer Ending, but twists into a Bittersweet Ending. Roy loses all of his money after being conned by the three people that he loves and trusts most, and he finds out that his daughter (who he owes his newfound happiness to) isn't really his daughter. Fast-forward one year: Despite all that's happened to him, Roy has successfully left his criminal past behind and conquered his neurosis, and he has a steady relationship with a woman he loves. When he encounters "Angela" again, he doesn't hold a grudge against her.

Evil Parents Want Good Kids: Roy, despite his long and checkered past, is appalled when he learns Angela isn't a innocent little waif; he is repeatedly shocked at her poor study habits, juvenile delinquency, and eagerness for con jobs.

Angela: "Teach me something! A con." Roy: "I'm not teaching you anything." Angela: "Why not?" Roy: "Because you're far too bright and innocent and beautiful and I'm not going to screw that up like everything else."

Massive Multiplayer Scam: Roy thinks he is working with Frank to take Chuck Frechette for $80,000. In reality, Frank, Angela, Dr. Klein, and several other accomplices are all working together to take Roy for the million-plus in his safe deposit box.

Neat Freak/Super OCD: Roy is obsessive with cleanliness — he can't stand to be outdoors, insists his visitors remove their shoes, opens and closes the front and back door three times, and spends an entire day cleaning the house out of fear it may be dirty.

Parental Hypocrisy: Roy the Con Man is strongly opposed to teaching Angela his tricks of the trade, and makes her return the takings of her first scam.

Roy: "I told you I'd teach you a con. I didn't say I'd let you get away with it."

Placebo Effect: Roy finds out that Dr. Klein's pills are actually soy menopause supplements, which he gave to Roy to prove that he didn't need pills to conquer his OCD. Roy realizes that bonding with Angela has given his life meaning and helped him overcome his neurosis.

Violin Scam: Roy uses two variations of this scam, one with a water filtration system (the mark buys it to avoid paying taxes for a nonexistent European vacation), and one with a "winning" lottery ticket.

You See, I'm Dying: Parodied. In the scene where Roy refuses to answer his phone while he's cleaning, Frank keeps leaving him voicemail messages trying to snap him out of it. After he's been at it for a few hours, he half-heartedly tries to guilt-trip Roy into picking up the phone by claiming that he's dying.

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